Vitamin B12

Base Information

• Chemical Name: Vitamin B12
• CAS No.: 68-19-9
• Molecular Formula: C63H88CoN14O14P
• Molecular Weight: 1355.44
• Hs Code.: 2936.26
• European Community (EC) Number: 236-500-2
• Wikipedia: Vitamin B12,Vitamin_B12
• NCI Thesaurus Code: C939
• RXCUI: 11248
• Metabolomics Workbench ID: 50451
• Mol file: 68-19-9.mol

Synonyms:Rubramin PC;Dodex;Betaline-12;Cotel;Byladoce;Depinar;Anacobin;Betalin 12, crystalline;Cyanobalamin concentrate;Plecyamin;Cabadon M;Cycobemin;Distivit (B12 peptide);Dodecabee;Embiol;Cyanocob(III)alamin;Crystimin;component of Endoglobin;Rubripca;Redisol;Cynobal;Dicopac;Cyanocobalamin (JP14/USP);Hemomin;Cytacon;Virubra;Erythrotin;CN-Cbl;5, 6-Dimethylbenzimidazolylcobamide cyanide;Factor II (vitamin);component of Vitron-C-Plus;Vitral;Cyredin;Prestwick_564;Cobalamin, cyanide;Coobalamed;CN-B12;Cytamen;Crystwel;Hepagon;Cykobemin;Euhaemon;Nagravon;Dodecavite;Vitarubin;Crystamine;Covit;Vitamin B12b;Cyomin;Cosmo-Rey;Cobione;Docemine;Redamina;SRI 2215;Cobinamide, cyanide hydroxide, dihydrogen phosphate;Vita-rubra;Cobadoce Forte;Poyamin;Fresmin;Factor II (vitamin B12);Erycytol;Bevidox;Hemo-b-doze;Cobamin;Normocytin;Biocobalamine;vitamin B-12;Dimethylbenzimidazoylcobamide;Hepcovite;Cobamide, .alpha.-5,6-dimethyl-1H-benzimidazolyl-, cyanide;B-Twelv-Ora;VB12;Vitamin B 12;Cobalin;Vitamin B12 preparation;Vibalt;Macrabin;Rebramin;cyano-5,6-dimethylbenzimidazole-;Vi-Twel;Rhodacryst;Cobalamin, cyano-;Cyomin (TN);Cyanocobalamine;LLD factor;Lactobacillus lactis dorner factor;Cykobeminet;Bevidox concentrate;Rubramin;Docigram;Dobetin;Betolvex;Vitamin B12 complex;Pernaevit;Factor II;Cyanocobalamin （Vitamin B12）;

Chemical Property of Vitamin B12

Chemical Property:

• Appearance/Colour: Crystalline
• Melting Point: >300 °C
• Boiling Point: >300 °C
• PKA: pKa 3.28±0.04(H2O,D2O t=23±0.5 Iunspeci?ed) (Uncertain)
• Flash Point: 9℃
• PSA: 459.72000
• LogP: 5.61808
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Soluble
• Water Solubility.: Soluble
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 16
• Exact Mass: 1328.564325
• Heavy Atom Count: 91
• Complexity: 3150

Purity/Quality:

99% ^*data from raw suppliers

VB12 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 22-24/25-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Vitamins and Derivatives
• Canonical SMILES: CC1=CC2=C(C=C1C)N(C=N2)C3C(C(C(O3)CO)OP(=O)([O-])OC(C)CNC(=O)CCC4(C(C5C6(C(C(C(=N6)C(=C7C(C(C(=N7)C=C8C(C(C(=N8)C(=C4[N-]5)C)CCC(=O)N)(C)C)CCC(=O)N)(C)CC(=O)N)C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.[Co]
• Isomeric SMILES: CC1=CC2=C(C=C1C)N(C=N2)[C@@H]3[C@@H]([C@@H]([C@H](O3)CO)OP(=O)([O-])O[C@H](C)CNC(=O)CC[C@@]\4([C@H]([C@@H]5[C@]6([C@@]([C@@H](C(=N6)/C(=C\7/[C@@]([C@@H](C(=N7)/C=C\8/C([C@@H](C(=N8)/C(=C4\[N-]5)/C)CCC(=O)N)(C)C)CCC(=O)N)(C)CC(=O)N)/C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.[Co]
• Recent ClinicalTrials: Testing the Use of Combination Immunotherapy Treatment (N-803 [ALT-803] Plus Pembrolizumab) Against the Usual Treatment for Advanced Non-small Cell Lung Cancer (A Lung-MAP Treatment Trial)
• Recent EU Clinical Trials: Open, Randomised Phase II Study Assessing The Toxicity And Efficacy Of Platinum-Based Chemotherapy With Vitamin Supplementation In The Treatment Of Lung Cancer
• Structure and Mechanisms: Vitamin B12 is a water-soluble vitamin with a complex structure. Its assimilation and transportation mechanisms involve three main proteins: intrinsic factor (IF), haptocorrin (HC), and transcobalamin (TC), along with their respective membrane receptors.
• Clinical Manifestations of Deficiency: B12 deficiency due to malabsorption can lead to various clinical symptoms, including hematological manifestations such as macrocytosis and megaloblastic anemia, central and peripheral neurological disorders, psychiatric disorders, and thromboembolic outcomes.
• Causes of Deficiency: Causes of B12 deficiency include malabsorption, defects in cellular delivery and uptake, and limited dietary intake. Disruption of B12-dependent reactions like the cytosolic methionine synthase reaction and mitochondrial methymalonyl CoA mutase reaction can lead to deficiency.
• Prevalence and Consequences: B12 deficiency is widespread across all age groups, especially in populations facing food insecurity. The consequences of deficiency can affect major organ systems including the blood, bone marrow, and nervous system, leading to conditions like megaloblastic anemia, nervous system disorders, cognitive impairment, and psychosis.
• Metabolic Roles and Health Implications: Vitamin B12 plays crucial metabolic roles throughout life, especially during pregnancy and early development. Evidence links B12 deficiency with increased risk of various neuro, vascular, immune, and inflammatory disorders.
• Unique Properties and Pathways: B12 has unique properties including a complex absorption and assimilation pathway requiring intact gastric and terminal small intestinal function, an enterohepatic pathway, and specific binding proteins and chaperones.
• Sources and Synthesis: B12 is synthesized only by microorganisms like bacteria, yeasts, and possibly some algae. Ruminant herbivores and certain monogastric animals host these bacteria in their intestines, explaining why they don't develop B12 deficiency despite lacking it in their food intake.

Technology Process of Vitamin B12

There total 2 articles about Vitamin B12 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 30.0%

methylcobalamine + 2,3-dicyano-5,6-dichloro-p-benzoquinone (84-58-2) → vitamin B-12 (68-19-9,32627-64-8,89138-85-2,41325-63-7,8039-03-0)

Guidance literature:

In ethanol; on react. of methyl cobalamine with soln. of 2,3-dichloro-5,6-dicyano-benzoquinone-(1,4) at darkness, 30min;;

Reference yield:

→ Cyanocobalamin (Vitamin B12) (68-19-9)

Guidance literature:

Faktor V(1a) (Cobyrinsaeure-abcdeg-hexamid), < 1-α-D-Rubofuranosyl-5,6-dimethyl-benzimidazol>-3'-;

DOI:10.1002/hlca.19600430314

Reference yield: 85.0%

cyanocobalamin (68-19-9) + trimethyloxosulfonium bromide (25596-24-1) → CH3Cb1 (13422-55-4)

Guidance literature:

cyanocobalamin; With sodium tetrahydroborate; cobalt(II) chloride; In water; butanone; at 30 - 50 ℃; for 1.66667 - 2.5h;

trimethyloxosulfonium bromide; In water; butanone; at 15 - 50 ℃;

upstream raw materials:

2,3-dicyano-5,6-dichloro-p-benzoquinone

Downstream raw materials:

CH₃Cb₁

dimethylsulfide

Refernces

Aromatic and benzylic C-H bond activation in the system bis(dicarbonylrhodium(I))porphyrinate-hydrocarbon solvent

10.1021/ic0011112

The research investigates the activation of aromatic and benzylic C-H bonds in the system involving bis(dicarbonylrhodium(I))porphyrinate-hydrocarbon solvent. The study aims to understand the reactivity of Rhodium (Rh) complexes with different oxidation states (RhI, RhII, and RhIII) towards C-H bonds, particularly focusing on the differences in reactivity between monometallic and bimetallic Rh complexes. The researchers used various porphyrin complexes, including Rh2(CO)4(por) (where por represents different porphyrin dianions such as OEP or TPP), RhIII(OEP)(PF6), and RhIII(TPP)(O2), along with hydrocarbon solvents like benzene, toluene, and anisole. The conclusions drawn from the study suggest that the activation of aromatic and benzylic C-H bonds in Rh2(CO)4(por) systems at elevated temperatures is attributed to RhII(por) and RhIII(por) derivatives, rather than the intrinsic reactivity of Rh2(CO)4(por) itself. The research provides insights into the potential for designing better catalysts and offers a synthetic route to organometallic RhIII(por) species, which are relevant to the reactivity of cobalamine in vitamin B12.

Reductive Radical Cyclisations of Bromo Acetals and (Bromomethyl)silyl Ethers of Terpenoid Alcohols

10.1002/hlca.19910740117

The research investigates the reductive radical cyclisation of bromo acetals and (bromomethyl)silyl ethers of terpenoid alcohols, aiming to explore the cyclisation pathways and products of these compounds under radical conditions. The study employs tin hydride and vitamin B12-catalysed methods to generate radicals, focusing on how different precursors influence cyclisation outcomes. Key chemicals include 2-bromo-acetaldehyde acetals, (2-bromomethyl)dimethylsilyl ethers, Bu3SnH for the tin hydride method, and vitamin B12 (hydroxocobalamine hydrochloride) for the light-assisted electrochemical reduction. The results show that bromo acetals predominantly undergo 5-'exo' cyclisation to form oxolanes, while (bromomethyl)silyl ethers exhibit more complex cyclisation patterns, including sequential 6-'endo' + 5-'exo' tandem cyclisation and triple cyclisation, leading to bicyclic and tricyclic products. The study concludes that the nature of olefinic bonds and the presence of heteroatoms significantly affect cyclisation pathways, providing insights into the mechanisms of radical cyclisation in these systems and highlighting the potential for further exploration of extended linear polyenes.